EP0074121A1 - Dérivés de 2,3,4,5-tétrahydro-1-benzoxépine-3,5-dione et leur procédé de préparation - Google Patents
Dérivés de 2,3,4,5-tétrahydro-1-benzoxépine-3,5-dione et leur procédé de préparation Download PDFInfo
- Publication number
- EP0074121A1 EP0074121A1 EP82108303A EP82108303A EP0074121A1 EP 0074121 A1 EP0074121 A1 EP 0074121A1 EP 82108303 A EP82108303 A EP 82108303A EP 82108303 A EP82108303 A EP 82108303A EP 0074121 A1 EP0074121 A1 EP 0074121A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- tetrahydro
- benzoxepine
- alkyl
- formula
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D313/08—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
Definitions
- the invention relates to the production of 2,3,4,5-tetrahydro-1-benzoxepine-3,5-dione derivatives and new 2,3,4,5-tetrahydro-1-benzoxepine-3,5 which can be prepared by this process -dione derivatives.
- the present invention has for its object to develop intermediates for the preparation of new compounds with valuable pharmacological and therapeutic properties and methods for the preparation of these intermediates.
- the invention therefore relates to new 2,3,4,5-tetrahydro-1-benzoxepine-3,5-dione derivatives of the formula I a wherein R 'and R 2 ' independently of one another each halogen or an alkyl, alkoxy or alkylthio group or one of the two radicals R 1 'and R 2 ' halogen or an alkyl, alkoxy, alkylthio, trifluoromethyl or nitro group and others may be hydrogen, the alkyl group each having 1 to 4 carbon atoms, except that when R 1 'is bromine R 2 ' is not methyl.
- the compounds represent valuable new intermediates for the manufacture of pharmaceuticals.
- Halogen atoms which can be used for the substituents R 1 and R 2 on the phenyl ring are fluorine, chlorine, bromine or iodine atoms, in particular fluorine, chlorine or bromine atoms.
- the C 1 - to C 4 -alkyl radicals in the alkyl, alkoxy or alkylthio groups can be straight or branched, and for example methyl, ethyl, propyl, isopropyl, butyl, isobutyl or tert. Represent butyl. In this case, especially in the case of multiple substitution on the phenyl radical, groups containing a carbon atom, such as methyl, methoxy or methylthio groups, are preferred.
- the invention further relates to a process for the preparation of 2,3,4,5-tetrahydro-1-benzoxepine-3,5-dione derivatives of the formula I.
- R 1 and R 2 each independently represent hydrogen, halogen or an alkyl, alkoxy or alkylthio group, where the alkyl radical can each have 1 to 4 carbon atoms, or one of the two radicals R 1 and R 2 a trifluoromethyl or nitro group and the other are hydrogen, characterized in that compounds of the formula II in which R and R 2 have the above meaning and R 3 is a straight or branched low molecular weight alkyl group, preferably a methyl group, with a strong base from the series lithium hydride, sodium hydride, lithium tert-butoxide or potassium tert-butoxide in the presence an inert solvent at temperatures between -70 ° C and the boiling point of the solvent.
- suitable solvents are dimethylformamide or tetrahydrofuran.
- the reaction mixture can be mixed with ice water and the precipitated compound of the formula I can be separated off.
- the compounds of the formula I can also be separated from the by-products by precipitation of the alkali metal salts, in particular the lithium salt, with a non-polar solvent, for example toluene or petroleum ether.
- the free compound can be released from the salt by means of an inorganic or organic acid, for example an aqueous solution of hydrochloric acid, sulfuric acid or acetic acid.
- the 2,3,4,5-tetrahydro-1-benzoxepine-3,5-dione compounds of the formula I can be reacted directly with amines, e.g. lower mono- or dialkylamines or lower N- (dialkyl) alkylenediamines, are converted into corresponding 3-amino-1-benzoxepin-5 (2H) -one compounds.
- the reaction can be carried out in a manner known per se in an inert solvent and can be promoted by adding catalytic amounts of an acid.
- the compounds of the formula I can also first be converted into the corresponding 3-halo-1-benzoxepin-5 (2H) -one compounds by treatment with an acid chloride such as oxalyl chloride and these can then be reacted further with an amine in a manner known per se .
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2931398 | 1979-08-02 | ||
DE19792931398 DE2931398A1 (de) | 1979-08-02 | 1979-08-02 | Neue 1-benzoxepin-5(2h)-on-derivate und ihre salze, verfahren und zwischenprodukte zu deren herstellung und diese verbindungen enthaltende arzneimittel |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP80104466.0 Division | 1980-07-29 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0074121A1 true EP0074121A1 (fr) | 1983-03-16 |
EP0074121B1 EP0074121B1 (fr) | 1985-04-10 |
Family
ID=6077477
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP80104466A Expired EP0025109B1 (fr) | 1979-08-02 | 1980-07-29 | Dérivés de 1-benzoxépin-5(2H)-ones et leurs sels, et procédés pour leur préparation |
EP82108303A Expired EP0074121B1 (fr) | 1979-08-02 | 1980-07-29 | Dérivés de 2,3,4,5-tétrahydro-1-benzoxépine-3,5-dione et leur procédé de préparation |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP80104466A Expired EP0025109B1 (fr) | 1979-08-02 | 1980-07-29 | Dérivés de 1-benzoxépin-5(2H)-ones et leurs sels, et procédés pour leur préparation |
Country Status (20)
Country | Link |
---|---|
US (2) | US4279905A (fr) |
EP (2) | EP0025109B1 (fr) |
JP (2) | JPS5653675A (fr) |
AU (1) | AU537110B2 (fr) |
CA (1) | CA1162553A (fr) |
DD (2) | DD154487A5 (fr) |
DE (3) | DE2931398A1 (fr) |
DK (2) | DK151629C (fr) |
ES (2) | ES493927A0 (fr) |
FI (1) | FI77029C (fr) |
GR (1) | GR69360B (fr) |
HU (2) | HU181580B (fr) |
IE (1) | IE50059B1 (fr) |
IL (1) | IL60557A (fr) |
NO (1) | NO155054C (fr) |
NZ (1) | NZ194331A (fr) |
PH (2) | PH16306A (fr) |
PT (1) | PT71599A (fr) |
SU (2) | SU955860A3 (fr) |
ZA (1) | ZA804546B (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2072484A1 (fr) | 2004-06-01 | 2009-06-24 | ExxonMobil Chemical Patents Inc. | Procédé d'oligomérisation d'oléfines |
WO2019118230A1 (fr) | 2017-12-14 | 2019-06-20 | Exxonmobil Chemical Patents Inc. | Procédés d'isomérisation d'alpha-oléfines |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3440296A1 (de) * | 1984-11-05 | 1986-05-15 | Kali-Chemie Pharma Gmbh, 3000 Hannover | 3-amino-2,3-dihydro-1-benzoxepin-verbindungen sowie verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
DE3440295A1 (de) * | 1984-11-05 | 1986-05-15 | Kali-Chemie Pharma Gmbh, 3000 Hannover | Verfahren zur diastereoselektiven reduktion von 3-amino-1-benzoxepin-5(2h)-onen |
JP4916481B2 (ja) * | 2008-05-27 | 2012-04-11 | ティーオーエー株式会社 | 機器筐体 |
WO2010077976A2 (fr) | 2008-12-17 | 2010-07-08 | The Regents Of The University Of California | Antagoniste du récepteur de la prokinéticine et ses utilisations |
US8718544B2 (en) | 2009-08-31 | 2014-05-06 | Sony Corporation | Signal transmission device, electronic device, and signal transmission method |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1593760A1 (de) * | 1967-02-01 | 1972-06-08 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung neuer Benz-epinderivate |
US3991082A (en) * | 1975-03-03 | 1976-11-09 | Warner-Lambert Company | 4-Substituted-2,3-dihydro-1-benzoxepin-3,5-diones and tautomers |
US4153612A (en) * | 1977-10-31 | 1979-05-08 | The Upjohn Company | 2-Benzoxepins |
-
1979
- 1979-08-02 DE DE19792931398 patent/DE2931398A1/de not_active Withdrawn
-
1980
- 1980-07-03 IE IE1387/80A patent/IE50059B1/en unknown
- 1980-07-11 IL IL60557A patent/IL60557A/xx unknown
- 1980-07-11 NZ NZ194331A patent/NZ194331A/xx unknown
- 1980-07-14 AU AU60389/80A patent/AU537110B2/en not_active Ceased
- 1980-07-16 PH PH24299A patent/PH16306A/en unknown
- 1980-07-24 PT PT71599A patent/PT71599A/pt unknown
- 1980-07-25 SU SU802950853A patent/SU955860A3/ru active
- 1980-07-28 US US06/173,076 patent/US4279905A/en not_active Expired - Lifetime
- 1980-07-28 ZA ZA00804546A patent/ZA804546B/xx unknown
- 1980-07-29 DE DE8282108303T patent/DE3070495D1/de not_active Expired
- 1980-07-29 EP EP80104466A patent/EP0025109B1/fr not_active Expired
- 1980-07-29 DE DE8080104466T patent/DE3070642D1/de not_active Expired
- 1980-07-29 EP EP82108303A patent/EP0074121B1/fr not_active Expired
- 1980-07-29 HU HU801890A patent/HU181580B/hu unknown
- 1980-07-29 HU HU821782A patent/HU182436B/hu unknown
- 1980-07-30 DD DD80222971A patent/DD154487A5/de unknown
- 1980-07-30 FI FI802385A patent/FI77029C/fi not_active IP Right Cessation
- 1980-07-30 DD DD80237321A patent/DD201792A5/de unknown
- 1980-07-31 GR GR62578A patent/GR69360B/el unknown
- 1980-08-01 DK DK333280A patent/DK151629C/da not_active IP Right Cessation
- 1980-08-01 JP JP10515980A patent/JPS5653675A/ja active Granted
- 1980-08-01 ES ES493927A patent/ES493927A0/es active Granted
- 1980-08-01 CA CA000357544A patent/CA1162553A/fr not_active Expired
- 1980-08-01 NO NO802324A patent/NO155054C/no unknown
-
1981
- 1981-03-16 US US06/243,745 patent/US4320061A/en not_active Expired - Lifetime
- 1981-04-09 ES ES501213A patent/ES8203875A1/es not_active Expired
- 1981-06-11 SU SU813294901A patent/SU963468A3/ru active
- 1981-11-27 PH PH26551A patent/PH17306A/en unknown
-
1988
- 1988-02-19 DK DK086188A patent/DK154081C/da active
-
1989
- 1989-03-16 JP JP1062356A patent/JPH0256478A/ja active Granted
Non-Patent Citations (4)
Title |
---|
CHEMICAL ABSTRACTS, Band 66, Nr. 5, 30. Januar 1967, Seite 1801, Spalte 1, Nr. 18659u, Columbus, Ohio, USA * |
CHEMICAL ABSTRACTS, Band 66, Nr. 5, 30. Januar 1967, Seite 1801, Spalte 1, Nr. 18659u, Columbus, Ohio, USA, J.H.P. TYMAN et al.: "Novel preparation of 1-benzoxepins" * |
THE JOURNAL OF ORGANIC CHEMISTRY, Band 42, Nr. 25, 9. Dezember 1977, Seiten 4265-4266 * |
THE JOURNAL OF ORGANIC CHEMISTRY, Band 42, Nr. 25, 9. Dezember 1977, Seiten 4265-4266, B.K. WASSON et al.: "A synthesis of 6-hydroxy-1-benzoxepin-3,5(2H,AH)-dione" * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2072484A1 (fr) | 2004-06-01 | 2009-06-24 | ExxonMobil Chemical Patents Inc. | Procédé d'oligomérisation d'oléfines |
WO2019118230A1 (fr) | 2017-12-14 | 2019-06-20 | Exxonmobil Chemical Patents Inc. | Procédés d'isomérisation d'alpha-oléfines |
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